Helional

Last updated
Helional
Ocean propanal.svg
Names
IUPAC name
3-(1,3-Benzodioxol-5-yl)-2-methylpropanal
Other names
2-Methyl-3-(3,4-methylenedioxyphenyl)propanal;
2-piperonylpropanal
Helional
Ocean propanal
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.528 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C11H12O3/c1-8(6-12)4-9-2-3-10-11(5-9)14-7-13-10/h2-3,5-6,8H,4,7H2,1H3
    Key: BOPPSUHPZARXTH-UHFFFAOYSA-N
  • InChI=1/C11H12O3/c1-8(6-12)4-9-2-3-10-11(5-9)14-7-13-10/h2-3,5-6,8H,4,7H2,1H3
    Key: BOPPSUHPZARXTH-UHFFFAOYAR
  • CC(CC1=CC2=C(C=C1)OCO2)C=O
Properties
C11H12O3
Molar mass 192.214 g·mol−1
AppearanceColorless liquid
Odor floral, herbaceous
Density 1.162 g/cm3
Boiling point 282 °C (540 °F; 555 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P305+P351+P338
Safety data sheet (SDS) [1]
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Helional (from heliotropin, from which is it commonly derived) is a chemical compound used as a perfume in soap and laundry detergent. Chemically it is an aldehyde with a hydrocinnamaldehyde motif; a structural element which is present in a number of other important commercial fragrances and odorants. [3]

Contents

Synthesis

Several synthetic routes exist but the most common is a crossed-aldol condensation between piperonal (heliotropin) and propanal followed by selective hydrogenation of the intermediate alkene. This produces a racemic product.

See also

References

  1. ↑ Sigma-Aldrich Co., 2-methyl-3-(3,4-methylenedioxyphenyl)propanal. Retrieved on 2016-03-02.
  2. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. ↑ Wetzel, Christian H.; Oles, Markus; Wellerdieck, Christiane; Kuczkowiak, Michael; Gisselmann, Gunter; Hatt, Hanns (1999). "Specificity and sensitivity of a human olfactory receptor functionally expressed in human embryonic kidney 293 cells and Xenopus laevis oocytes". Journal of Neuroscience. 19 (1): 7426–7433. doi: 10.1093/chemse/bji002 . PMID   15647465.


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